1-(2-nitrobenzyl)-1H-pyrrole-2-carbaldehyde → 10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

HRID 1290903노트

반응식

HRID 1290903 반응식
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=O)([O-])=O>C(OCC)(=O)C.C(O)C.C(Cl)Cl.[Pd]>[CH:9]1[CH:10]=[CH:11][N:7]2[CH2:6][C:5]3[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=3[NH:1][CH2:12][C:8]=12

참가 물질

6

반응물 1

HCID 7362171-(2-nitrobenzyl)-1H-pyrrole-2-carbaldehyde

생성물 1

HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine수율 66.6%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 702Ethanol용매2회HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 30.6 g of 1-(2-nitrobenzyl)-2-pyrrolecarboxaldehyde and 3.06 g of 10% Pd/C in 400 ml of ethyl acetate and 400 ml of ethyl alcohol is hydrogenated over 18 hours. The reaction mixture is filtered through diatomaceous earth and the filtrate is treated with activated carbon and filtered through diatomaceous earth. The filtrate is concentrated in vacuo to give a residue which is dissolved in methylene chloride containing ethyl alcohol. The solution is passed through a pad of silica gel and the pad washed with a 7:1 hexane-ethyl acetate solution to give 16.31 g of the desired product as solid, m.p. 145°-148° C.

후처리

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. additionthe filtrate is treated with activated carbon
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto give a residue which
  6. washthe pad washed with a 7:1 hexane-ethyl acetate solution

출처 및 근거

ORD 기록
ord-d9f821047e814f8cb7b8d3e15eef1c2c
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753648

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